Dimethylformamide → Methyl 4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

HRID 1433516Notes

Reaction equation

HRID 1433516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[NH:28][C:29]([O:31]C1C=CC=CC=1)=O)[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=2)[N:9]=[CH:8][CH:7]=1.[CH:38]1([NH2:41])[CH2:40][CH2:39]1.CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[NH:28][C:29]([NH:41][CH:38]1[CH2:40][CH2:39]1)=[O:31])[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 58931268Methyl 4-(3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Product 1

HCID 58931300Methyl 4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-[3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate (3.2 g), cyclopropylamine (1.3 ml) and dimethylformamide (20 ml) were stirred together at 60° C. for 10 minutes. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=50:1, 20:1) to obtain 2.26 g of the target substance as a white powder.

Workup

  1. customwas returned to room temperature
  2. extractionextraction
  3. additionSilica gel was added to the extract solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with silica gel, and purification
  7. customto obtain 2.26 g of the target substance as a white powder

Sources & evidence

ORD record
ord-89f28ba44a1f4e3c9b14bd3ab5a4b927
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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